JP2000502046A - 殺虫特性を有するアシル化５−アミノイソチアゾール類、それを製造するための中間体生成物および方法 - Google Patents

殺虫特性を有するアシル化５−アミノイソチアゾール類、それを製造するための中間体生成物および方法

Info

Publication number: JP2000502046A
Authority: JP; Japan
Prior art keywords: fluorine; atoms; alkyl; formula; same
Prior art date: 1995-11-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Ceased

Application number

JP9518545A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000502046A5 (zh

Inventor

ハイル，マルクス

エルデレン，クリストフ

バヘンドルフ−ノイマン，ウルリケ

トウルベルク，アンドレアス

メンケ，ノルベルト

Original Assignee

バイエル・アクチエンゲゼルシヤフト

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-11-14

Filing date

1996-11-04

Publication date

2000-02-22

1996-11-04 Application filed by バイエル・アクチエンゲゼルシヤフト filed Critical バイエル・アクチエンゲゼルシヤフト

2000-02-22 Publication of JP2000502046A publication Critical patent/JP2000502046A/ja

2005-02-10 Publication of JP2000502046A5 publication Critical patent/JP2000502046A5/ja

Status Ceased legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 36
GKZNVLJEHYUFIC-UHFFFAOYSA-N 1,2-thiazol-5-amine Chemical class NC1=CC=NS1 GKZNVLJEHYUFIC-UHFFFAOYSA-N 0.000 title claims abstract description 15
239000013067 intermediate product Substances 0.000 title abstract description 3
230000000749 insecticidal effect Effects 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 144
241000607479 Yersinia pestis Species 0.000 claims abstract description 14
-1 alkylthioal Kill Chemical group 0.000 claims description 89
239000011737 fluorine Substances 0.000 claims description 62
229910052731 fluorine Inorganic materials 0.000 claims description 62
239000000460 chlorine Chemical group 0.000 claims description 56
125000005843 halogen group Chemical group 0.000 claims description 55
229910052801 chlorine Inorganic materials 0.000 claims description 48
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 32
229910052736 halogen Inorganic materials 0.000 claims description 29
150000002367 halogens Chemical class 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 22
125000001309 chloro group Chemical group Cl* 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
239000003085 diluting agent Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
238000002156 mixing Methods 0.000 claims description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
230000000802 nitrating effect Effects 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
IJUDUPSHUGIGMT-IHWYPQMZSA-N (z)-3-aminobut-2-enethioamide Chemical class C\C(N)=C\C(N)=S IJUDUPSHUGIGMT-IHWYPQMZSA-N 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
239000004067 bulking agent Substances 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000004450 alkenylene group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 19
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 2
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
125000004965 chloroalkyl group Chemical group 0.000 claims 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000000858 thiocyanato group Chemical group *SC#N 0.000 claims 1
238000002360 preparation method Methods 0.000 description 54
239000002904 solvent Substances 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
238000012360 testing method Methods 0.000 description 34
239000003995 emulsifying agent Substances 0.000 description 29
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000000126 substance Substances 0.000 description 20
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239000012141 concentrate Substances 0.000 description 16
235000008504 concentrate Nutrition 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
230000000694 effects Effects 0.000 description 13
241000238876 Acari Species 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
229920000151 polyglycol Polymers 0.000 description 12
239000010695 polyglycol Substances 0.000 description 12
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239000000417 fungicide Substances 0.000 description 11
239000002023 wood Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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239000011230 binding agent Substances 0.000 description 10
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
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MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
PQFRTXSWDXZRRS-UHFFFAOYSA-N ronidazole Chemical compound CN1C(COC(N)=O)=NC=C1[N+]([O-])=O PQFRTXSWDXZRRS-UHFFFAOYSA-N 0.000 description 1
235000013533 rum Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
201000010153 skin papilloma Diseases 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
239000008279 sol Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229940074152 thuringiensin Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1
WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Chemical class 0.000 description 1
239000011701 zinc Chemical class 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
- C07C233/91—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated with carbon atoms of the carboxamide groups bound to acyclic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

JP9518545A 1995-11-14 1996-11-04 殺虫特性を有するアシル化５−アミノイソチアゾール類、それを製造するための中間体生成物および方法 Ceased JP2000502046A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19542372A DE19542372A1 (de)	1995-11-14	1995-11-14	Acylierte 5-Aminoisothiazole
DE19542372.0		1995-11-14
PCT/EP1996/004796 WO1997018198A1 (de)	1995-11-14	1996-11-04	Acylierte 5-aminoisothiazole mit insektizider wirkung, zwischenprodukte und verfahren zu ihrer herstellung

Publications (2)

Publication Number	Publication Date
JP2000502046A true JP2000502046A (ja)	2000-02-22
JP2000502046A5 JP2000502046A5 (zh)	2005-02-10

Family

ID=7777402

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9518545A Ceased JP2000502046A (ja)	1995-11-14	1996-11-04	殺虫特性を有するアシル化５−アミノイソチアゾール類、それを製造するための中間体生成物および方法

Country Status (15)

Country	Link
US (2)	US5972843A (zh)
EP (1)	EP0861241B1 (zh)
JP (1)	JP2000502046A (zh)
KR (1)	KR19990064325A (zh)
CN (1)	CN1071749C (zh)
AU (1)	AU7563396A (zh)
BR (1)	BR9611475A (zh)
DE (2)	DE19542372A1 (zh)
ES (1)	ES2215199T3 (zh)
HK (1)	HK1017675A1 (zh)
ID (1)	ID17719A (zh)
IL (1)	IL124022A (zh)
MX (1)	MX9803629A (zh)
TW (1)	TW343130B (zh)
WO (1)	WO1997018198A1 (zh)

Cited By (1)

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JP2002521480A (ja) *	1998-07-30	2002-07-16	シンジェンタリミテッド	ベンザゾール類：ベンズオキサゾール、ベンズチアゾール及びベンズイミダゾール誘導体類

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DE19628569A1 (de) *	1996-07-16	1998-01-22	Bayer Ag	Substituierte N-(5-Isothiazolyl)-thioamide
DE19727162A1 (de) *	1997-06-26	1999-01-07	Bayer Ag	Substituierte Aminoheterocyclylamide
DE19736545A1 (de) *	1997-08-22	1999-02-25	Bayer Ag	Acylierte 5-Aminoisothiazole
DE19846008A1 (de)	1998-10-06	2000-04-13	Bayer Ag	Phenylessigsäure-heterocyclylamide
US6320050B1 (en) *	1999-03-29	2001-11-20	Hoffmann-La Roche Inc.	Heteroaromatic glucokinase activators
US6610846B1 (en) *	1999-03-29	2003-08-26	Hoffman-La Roche Inc.	Heteroaromatic glucokinase activators
AU764228B2 (en) *	1999-11-18	2003-08-14	Novartis Ag	Pesticidal aminoheterocyclamide compounds
ATE259792T1 (de) *	1999-11-29	2004-03-15	Novartis Pharma Gmbh	Pestizide n-heteroaryl alpha- alkoximinocarbonsäureamide
WO2001046165A2 (en) *	1999-12-16	2001-06-28	Novartis Ag	N-heteroaryl-amides and their use as parasiticides
GB0002040D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002034D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
PE20010830A1 (es)	2000-01-28	2001-09-06	Syngenta Ltd	Derivados de azol insecticidas o fungicidas y composiciones que los comprenden
GB0002029D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002031D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002032D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002036D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
DE10015015A1 (de) *	2000-03-27	2001-10-04	Bayer Ag	Oxim-Derivate
US6667326B1 (en)	2000-11-16	2003-12-23	Novartis Animal Health Us, Inc.	Pesticidal aminoheterocyclamide compounds
AU2003296662A1 (en) *	2002-12-20	2004-07-22	Basf Aktiengesellschaft	Triazolopyrimidines, methods for the production thereof, use thereof for controlling harmful fungi, and substances containing said triazolopyrimidines
US20060135455A1 (en)	2004-06-01	2006-06-22	Reza Sheikhnejad	Methods and compositions for the inhibition of gene expression
EP1971371B1 (en)	2005-12-01	2015-08-05	Pronai Therapeutics, Inc.	Cancer therapies and pharmaceutical compositions used therein
BRPI0712862A2 (pt) *	2006-06-08	2012-12-18	Lilly Co Eli	carboxamidas substituìdas
US20150299803A1 (en)	2012-11-05	2015-10-22	Pronai Therapeutics, Inc.	Methods of Using Biomarkers for the Treatment of Cancer by Modulation of BCL2 Expression

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DE1924830A1 (de) *	1968-07-06	1970-11-19	Merck Patent Gmbh	Neues Verfahren zur Herstellung von 5-Acylamino-isothiazolderivaten
US4966908A (en) *	1988-03-21	1990-10-30	Ciba-Geigy Corporation	Isonicotinic acid amides for protecting plants against disease
JPH072604A (ja) *	1993-05-05	1995-01-06	Shell Internatl Res Maatschappij Bv	殺虫方法および農薬化合物
DE4328425A1 (de) *	1993-08-24	1995-03-02	Basf Ag	Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung
AU2641295A (en) *	1994-05-17	1995-12-05	Dowelanco	N-(5-isothiazolyl)amide pesticides

1995
- 1995-11-14 DE DE19542372A patent/DE19542372A1/de not_active Withdrawn
1996
- 1996-11-04 BR BR9611475A patent/BR9611475A/pt not_active IP Right Cessation
- 1996-11-04 CN CN96198283A patent/CN1071749C/zh not_active Expired - Fee Related
- 1996-11-04 AU AU75633/96A patent/AU7563396A/en not_active Abandoned
- 1996-11-04 JP JP9518545A patent/JP2000502046A/ja not_active Ceased
- 1996-11-04 US US09/068,598 patent/US5972843A/en not_active Expired - Fee Related
- 1996-11-04 ES ES96938067T patent/ES2215199T3/es not_active Expired - Lifetime
- 1996-11-04 EP EP96938067A patent/EP0861241B1/de not_active Expired - Lifetime
- 1996-11-04 IL IL12402296A patent/IL124022A/en not_active IP Right Cessation
- 1996-11-04 WO PCT/EP1996/004796 patent/WO1997018198A1/de active IP Right Grant
- 1996-11-04 DE DE59610983T patent/DE59610983D1/de not_active Expired - Fee Related
- 1996-11-04 KR KR1019980702824A patent/KR19990064325A/ko active IP Right Grant
- 1996-11-11 TW TW085113741A patent/TW343130B/zh active
- 1996-11-13 ID IDP963306A patent/ID17719A/id unknown
1998
- 1998-05-07 MX MX9803629A patent/MX9803629A/es unknown
1999
- 1999-05-19 HK HK99102223A patent/HK1017675A1/xx not_active IP Right Cessation
- 1999-06-22 US US09/338,484 patent/US6008366A/en not_active Expired - Fee Related

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002521480A (ja) *	1998-07-30	2002-07-16	シンジェンタリミテッド	ベンザゾール類：ベンズオキサゾール、ベンズチアゾール及びベンズイミダゾール誘導体類

Also Published As

Publication number	Publication date
EP0861241A1 (de)	1998-09-02
TW343130B (en)	1998-10-21
CN1202162A (zh)	1998-12-16
WO1997018198A1 (de)	1997-05-22
US5972843A (en)	1999-10-26
US6008366A (en)	1999-12-28
DE19542372A1 (de)	1997-05-15
IL124022A (en)	2001-05-20
KR19990064325A (ko)	1999-07-26
HK1017675A1 (en)	1999-11-26
BR9611475A (pt)	1999-07-13
AU7563396A (en)	1997-06-05
CN1071749C (zh)	2001-09-26
EP0861241B1 (de)	2004-04-14
MX9803629A (es)	1998-09-30
ES2215199T3 (es)	2004-10-01
DE59610983D1 (de)	2004-05-19
ID17719A (id)	1998-01-22

Publication	Publication Date	Title
JP4434317B2 (ja)	2010-03-17	有害生物防除剤としての３−チオカルバモイルピラゾール誘導体
US5972843A (en)	1999-10-26	Acylated 5-aminoisothiazoles with insecticidal properties, intermediate products and process for producing them
JP2000503998A (ja)	2000-04-04	アシル化された４―アミノ―及び４―ヒドラジノピリミジン及びその有害生物防除剤としての使用
AU712985B2 (en)	1999-11-18	Acylated 5-amino-1,2,4-thiadiazoles as pesticides and fungicides
US6258957B1 (en)	2001-07-10	N-aryl-1,2,4-triazolin-5-ones
US5973162A (en)	1999-10-26	Substituted thiazolines and their use for controlling animal pests
JP2000515135A (ja)	2000-11-14	置換されたｎ―（５―イソチアゾリル）チオアミド類
KR20000029574A (ko)	2000-05-25	치환ｎ-이소티아졸일-(티오)아미드
EP0970059B1 (de)	2003-08-20	Disubstituierte biphenyloxazoline
US5994551A (en)	1999-11-30	1-heterocyclyl methyl-2-nitro-or-cyanoiminidazoline salts, process for their preparation, pesticidal composition containing them, and pesticidal method of using them
JP2002507217A (ja)	2002-03-05	２−（２−メチルフェニル）−オキサゾリン
JP2001521535A (ja)	2001-11-06	殺虫作用を有する置換ジフェニルオキサゾリン誘導体
JPH10508592A (ja)	1998-08-25	フルオロブテニルエステル類および動物の有害生物を抑制するためのそれらの使用
AU8111198A (en)	1999-01-19	Substituted aminoheterocyclylamides
EP0944608B1 (de)	2003-04-16	4-cyclohexylphenyl-oxazoline und ihre verwendung zur bekämpfung von tierischen schädlingen
JP2001523667A (ja)	2001-11-27	縮合ピリジン誘導体
JP2001523664A (ja)	2001-11-27	有害生物防除剤及び殺菌・殺カビ剤としてのアシル化４−アミノピリジン誘導体
JP2001523665A (ja)	2001-11-27	有害生物防除剤および殺菌・殺カビ剤としてのアシル化された４−アミノピリジン類
MXPA99005160A (es)	2000-02-02	Derivados de 3-tiocarbamoilpirazol como pesticidas
MXPA99000423A (en)	1999-09-20	N- (5-isotiazolyl) -tioamides substitui
CA2245875A1 (en)	1997-08-21	Salts from imidazoline derivatives and their use as a parasite control agent
KR20000075506A (ko)	2000-12-15	이치환 비페닐옥사졸린

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2007-05-29	A131	Notification of reasons for refusal	Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070529
2007-11-08	A313	Final decision of rejection without a dissenting response from the applicant	Free format text: JAPANESE INTERMEDIATE CODE: A313 Effective date: 20071017
2007-11-27	A02	Decision of refusal	Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20071127

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2007-05-29

A131

Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20070529

2007-11-08

A313

Final decision of rejection without a dissenting response from the applicant

Free format text: JAPANESE INTERMEDIATE CODE: A313

Effective date: 20071017

2007-11-27

A02

Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20071127

JP2000502046A - 殺虫特性を有するアシル化５−アミノイソチアゾール類、それを製造するための中間体生成物および方法 - Google Patents

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